2775-87-3

Usage

Uses

Used in Organic Synthesis:
2,4(1H,3H)-Pyrimidinedione, 3-benzoylis used as a building block in organic synthesis for the preparation of various pharmaceuticals and agrochemicals. Its unique chemical structure allows for the creation of a wide range of compounds with diverse applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2,4(1H,3H)-Pyrimidinedione, 3-benzoylis utilized as a key intermediate for the synthesis of therapeutic agents. Its versatile chemical properties enable the development of new drugs with improved efficacy and safety profiles.
Used in Antiviral Applications:
2,4(1H,3H)-Pyrimidinedione, 3-benzoylhas been studied for its potential antiviral properties. It may be used as an antiviral agent to inhibit the replication of certain viruses, thereby providing a potential treatment for viral infections.
Used in Anticancer Applications:
2,4(1H,3H)-Pyrimidinedione, 3-benzoylhas also been investigated for its anticancer properties. 2,4(1H,3H)-Pyrimidinedione, 3-benzoylmay be employed as an anticancer agent, targeting specific cancer cells and inhibiting their growth and proliferation.
Used in Drug Delivery Systems:
To enhance the therapeutic potential of 2,4(1H,3H)-Pyrimidinedione, 3-benzoyl-, various drug delivery systems have been developed. These systems aim to improve the compound's bioavailability, delivery, and overall therapeutic outcomes, making it a more effective treatment option for various diseases and conditions.

Upstream product

• 98-88-4 benzoyl chloride 
• 66-22-8 uracil 
• 4330-14-7 1,3-dibenzoyluracil 

Downstream Products

• 13345-72-7 1-cyclopentyluracil 
• 138903-89-6 [(1R,3S)-3-(3-Benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopentyl]-acetic acid methyl ester 
• 138903-89-6 methyl cis-3-(3-benzoyl-1,2,3,4-tetrahydro-2,4-dioxopyrimidin-1-yl)cyclopentaneacetate 
• 66-22-8 uracil 
• 1053732-11-8 3-Benzoyl-1-((4aR,7S,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione 
• 183959-15-1 2,2-Dimethyl-propionic acid (2R,4S,5R)-2-(3-benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4,6-bis-benzyloxy-5-(2,2-dimethyl-propionyloxy)-hexyl ester 
• 191655-65-9 tert-butyl 7-(N³-benzoyluracil-1-yl)-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate 
• 207232-19-7 (2R,4R)-3-benzoyl-1-(2-tert-butyldiphenylsilyloxymethyl-3-methylene-tetrahydrofuran-4-yl)-1H-pyrimidine-2,4-dione 
• 215544-51-7 3-Benzoyl-1-(3-benzyloxymethyl-cyclobutyl)-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Synthesis of Flexible Difluorinated Cyclopropanoid Nucleoside Analogues

A novel class of difluorinated cyclopropanoic nucleoside analogues containing a hydroxypropyl group and a methylene spacer between the difluorocyclopropane ring and the heterocycle has been prepared.

Synthesis of difluorocyclopropyl carbocyclic homo-nucleosides

Racemic difluorinated carbocyclic homo-nucleoside analogues are easily accessible from (Z)-4-(benzyloxy)-2-butenyl acetate by difluorocyclopropanation using sodium chlorodifluoro acetate in diglyme at 190°C followed by Mitsunobu reactions.

Enantioselective synthesis of homo-N-nucleosides containing a 1,4-dioxane sugar analog

A dioxane homo-sugar analog, (2S,5S)-and (2R,5S)-5-[(4S)-2,2-dimethyl-1,3- dioxolan-4-yl]-2-iodomethyl-1,4-dioxane was prepared from (2R,3R)-dimethyl tartrate, and further elaborated into the corresponding homo-N-nucleoside analogs by its reactions with uracil and adenine, respectively.

Covalent Inhibition of Wild-Type HIV-1 Reverse Transcriptase Using a Fluorosulfate Warhead

Covalent inhibitors of wild-type HIV-1 reverse transcriptase (CRTIs) are reported. Three compounds derived from catechol diether non-nucleoside inhibitors (NNRTIs) with addition of a fluorosulfate warhead are demonstrated to covalently modify Tyr181 of HIV-RT. X-ray crystal structures for complexes of the CRTIs with the enzyme are provided, which fully demonstrate the covalent attachment, and confirmation is provided by appropriate mass shifts in ESI-TOF mass spectra. The three CRTIs and six noncovalent analogues are found to be potent inhibitors with both IC50 values for in vitro inhibition of WT RT and EC50 values for cytopathic protection of HIV-1-infected human T-cells in the 5-320 nM range.

Prolinamides of Aminouracils, Organocatalyst Modifiable by Complementary Modules

We report the synthesis and evaluation of prolinamide organocatalysts that incorporate aminouracils. The features of these catalysts are enhanced NH acidity of the amide because of the electron-withdrawing nature of the heterocycle, an additional hydrogen-bond donor at the α or β positions of this functional group (using 6-aminouracil or 5,6-diaminouracil respectively), and it can be recovered due to its low solubility and used again without decreasing the enantioselectivity. A unique feature of these systems is the self-assembly capability with complementary modules by Watson–Crick interactions. These supramolecular adducts behave differently from the catalyst alone, some of them have lower performance but others improve the selectivity of the product. Therefore, this approach avoids the synthesis of many catalysts.

Synthesis of 5,5-difluoro-5-phosphono-pent-2-en-1-yl nucleosides as potential antiviral agents

A series of hitherto unknown acyclic 5,5-difluoro-5-phosphono-pent-2-en-1-yl-pyrimidines (9a, b, 13a, b), -purines (16a, b) and -(1,2,4)-triazolo-3-carboxamide (19) were successfully synthesized from (E)-1-bromo-5-diethoxyphosphoryl-5,5-difluoro-pent-2-en

Discovery of uracil-bearing DAPYs derivatives as novel HIV-1 NNRTIs via crystallographic overlay-based molecular hybridization

A novel series of uracil-bearing DAPYs derivatives were designed and synthesized via structure-based molecular hybridization to discover compounds with improved anti-resistance profiles. Anti-HIV activity of the designed compounds was tested in MT-4 cell

Synthesis of Azacyclic Nucleoside Analogues via Asymmetric [3 + 2] Cycloaddition of 9-(2-Tosylvinyl)-9H -purines

With 9-(2-tosylvinyl)-9H-purines as the dipolarophiles, a series of chiral azacyclic nucleosides with four continuous stereocenters were obtained in 86-99% yields, >20:1 dr, and 94 → 99% ee via the Cu(I)-catalyzed asymmetric [3 + 2] cycloaddition. Both (E)- and (Z)-9-(2-tosylvinyl)-9H-purines were suitable dipolarophiles, enriching the structure diversity of azacyclic nucleosides. Furthermore, when α-methyl imino ester was explored, the corresponding azacyclic nucleoside with a chiral quaternary stereocenter could also be afforded with excellent results. (Chemical Equation Presented).

Discovery of New Acid Ceramidase-Targeted Acyclic 5-Alkynyl and 5-Heteroaryl Uracil Nucleosides

A series of novel N-acyclic uracil analogs with linear, branched, aromatic, and cyclopropyl-alkynyl as well as heteroaryl moieties at C-5 were prepared using palladium catalyzed Sonogashira and Stille cross-coupling and evaluated against malignant tumor cell lines. C-5-Furan-2-yl uracil derivative 6 was shown to be more potent against MCF-7 than the reference drug 5-fluorouracil (5-FU), while C-5-alkynyl uracil derivatives 9c and 9e exhibited antibreast cancer activities comparable to 5-FU. Selected compounds induced cell death, partially due to apoptosis, of MCF-7 breast cancer cells. Abrogation of acid ceramidase (ASAH1) expression of 9c and 9e indicated that these compounds could perturb ASAH1-mediated sphingolipid signaling. The selective activity of 9c and 9e against breast cancer cells via the ASAH1-mediated signaling, as a molecular target, might have a great advantage for potential future therapeutic use.

COMPOUNDS AND METHODS FOR TREATING HIV INFECTIONS

The present invention is directed to novel nanomolar and picomolar inhibitors of HIV reverse transcriptase, pharmaceutical compositions therefrom and methods for inhibiting reverse transcriptase and treating HIV infections, especially included drug resistant strains of HIV-1 and HIV-2 and/or secondary disease states and/or conditions which occur as a consequence of HIV infection.